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The 10 Best Hipster Bars in Chicago

With several different neighbourhoods on the rise at present, Chicago is absolutely bursting with trendy, inventive bars with a fantastic live music scene at its foundation.

This is, after all, the home of Pitchfork, so it makes perfect sense that so many hipsters have flocked to Chicago in the past decade. The bar scene of America's second city (or third, if you hail from LA) is a great example of old and new establishments combining well to make for a really vibrant and diverse scene. In our list we've aimed to include some of the veteran bars in their rightful place as well as acknowledging some intriguing newcomers. The future of Chicago's bar scene looks bright indeed.

10. Bar DeVille

This Ukrainian Village bar is fancier and more expensive than others on this list, but owners Matt and Kevin Heisner know who they’re providing for. This place is a chic cocktail lounge with definite nods to hipsterism in the form of its Art Deco-dive bar fusion design, stag antlers and its wide range of beers.

9. Simone’s

Located in the rising Pilsen neighbourhood, Simone’s is a lovely chill bar that serves up some amazing food. The herb garden out back, housed among graffiti-covered walls, is a particularly nice touch.

8. Innertown Pub

Its (very retro looking) sign announces it as a “Home to the arts”. Indeed, Innertown seems to purposely inaccurately define itself as a pub, perhaps to provide an extra element of surprise to first time visitors to this fun venue. Much more than drinking happens here. Expect space devoted to stuff like an arts and crafts market during the day and comedy routines at night. This is a buzzing bar cum community space.

7. East Room

East Room's charm comes from its hidden-away vibe. The entrance is thought an unmarked door in an alley just off Logan Square with a single red light above it. This very focus on obscurity indeed makes it one of the most talked about bars in the area. Make no mistake, despite being tucked away, this place isn’t exactly laid back: a dark, energetic dance floor, art house films projected onto the walls and cheap beer sold in cans combine to create a boisterous atmosphere.

6. Empty Bottle

Empty Bottle’s reputation for hosting up and coming acts is pretty much unimpeachable, any regular will tell you of the time they saw Arcade Fire take the stage before they become global festival darlings. This is a nice, relaxed spot for shooting pool over a few drinks. By day it also hosts a clothing and vinyl market.

5. Handlebar

A play (probably, surely?) on both the popular moustache among hipsters and the handlebars of a bike. This bar promotes some fairly obscure enough nights, like Bike Messenger Mondays, which offers free chips to bike messengers. The food menu is entirely vegan and the patio is chill, intimate place for a few cold drinks. Great ambiance every night of the week.

4. Burlington

A schedule of alternative acts playing every night of the week maintain a busting crowd of regulars. In recent years Burlington has bolstered its live music credentials by creating Neon Marshmallow Fest, which is staged at the same time as, and exists in opposition to, Lollapalooza Festival.

3. Rainbo Club

Once a favourite hangout of The Smashing Pumpkins, this famous dive bar looks like it’s still firmly stuck in the early 90s, which suits its loyal customers just fine. Rainbo has achieved the impressive feat of managing to remain relatively underground despite these famous associations.

2. Maria’s Packaged Goods

Maria's has firmly established itself as a favourite spot among hip, young Chicagoans. This is a very trendy establishment complete with an obscure, faux-blue collar name. Their resident DJs really know their stuff and the bar boasts an unbeatable range of craft beers (over 500). Maria's markets itself as a real community bar, strongly backed up by it also being home to the influential left-leaning arts and culture publication Lumpen.

1. The Whistler

The Whistler is an extremely versatile space and succeeds fantastically at doing multiple things right simultaneously – cocktail bar, art gallery, live music venue and even their own Whistler Records. This is arguably the type of place that every hipster bar the world over aspires to be. The Whistler avoids selling out by forcibly keeping the crowd small: the capacity of this place is less than 80 people (74 to be precise). This place is VIHP.